Lakeland - Winter Haven Short-Term Rentals from S$103: Search Holiday Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Lakeland - Winter Haven holiday rentals

A swimming pool with a fence, lounge chairs, and a palm tree.

1. Lake Ida Beach Resort

Winter Haven

Heather

includes taxes & fees

8 Nov - 9 Nov

A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

2. BlockHaven near Legoland & Disney

Winter Haven

Yuliett

includes taxes & fees

12 Nov - 13 Nov

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.

3. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Orlando

Julie

includes taxes & fees

30 Nov - 1 Dec

A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

4. Vacation Village Orlando, Celebration

Kissimmee

Desiree

includes taxes & fees

29 Nov - 30 Nov

A two-story house with a porch, surrounded by palm trees and greenery.

5. Barefoot'n Resort Kissimmee Orlando

Kissimmee

James

includes taxes & fees

1 Nov - 2 Nov

A riverside cabin with a dock, surrounded by lush greenery and a cloudy sky.

6. Camp Mack Lodge, Marina & RV Resort

Lake Wales

Terri

includes taxes & fees

2 Nov - 3 Nov

A swimming pool with lounge chairs and umbrellas, a covered seating area, and a building with a balcony in the background.

7. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Davenport

Lynn

includes taxes & fees

1 Nov - 2 Nov

8. Upstay 3BR Condo w Pool & Patio Near Disney

Winter Garden

includes taxes & fees

11 Nov - 12 Nov

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Lakeland - Winter Haven Hotel Reviews

The Berkley, Orlando

10/10 Excellent

"Very pleased overall"

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent

"The resort is perfectly located close to shopping and restaurants nice clean area and resort beautiful. Easy parking and would definitely stay again my only recommendation is to add a microwave in room since it had a dining room but no microwave didn’t make sense and place the room safe lower it was in closet on top shelf had to climb on top of bed to reach safe"

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"Pros :Our stay was amazing. Staff texted everyday to ensure we had everything we needed. Distances between our room and the grounds amenities was a bit far, so rides within the property were available within minutes with just a simple text. Our deposit was returned within hours of our departure. Cons: Hidden resort fees and parking fees arent' listed on hotels.com booking site. There isn't a designated smoking area on the site which was difficult for the smoker in our group."

Hilton Vacation Club Aqua Sol Orlando West

8/10 Good

"Our SECOND stay at Hilton Aqua Sol, and once again, we loved it! We made a last-minute reservation after leaving The Grove (just nine minutes away) due to a very disappointing experience there. Hilton reminded us why it’s our favorite! The hotel is beautiful, the renovations are lovely, and the staff is friendly. We especially love the heated pool by the lobby and all the family activities, including bikes, boat rides, the playground, and sandy play area. So much fun for the kids! A heads-up: We were surprised by the parking and additional service fees. Also, be careful with the timeshare/ownership offers. They attract you with points and complimentary nights, but there are conditions. We were told we’d lose a $100 credit card hold if we didn’t attend the presentation with our spouse and children. Don’t let the free nights or points pressure you into spending your vacation time on a presentation! Overall, we had a wonderful stay. Hilton Aqua Sol remains our favorite, and we will definitely be back next year!"

Explore a world of travel with Expedia

Florida Holiday Rentals

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lakeland - Winter Haven holiday rentals

1. Lake Ida Beach Resort

2. BlockHaven near Legoland & Disney

3. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4. Vacation Village Orlando, Celebration

5. Barefoot'n Resort Kissimmee Orlando

6. Camp Mack Lodge, Marina & RV Resort

7. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

8. Upstay 3BR Condo w Pool & Patio Near Disney

9. Lifetime of Vacations Resort

Find holiday rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

The Berkley, Orlando

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

Howard Johnson by Wyndham Lakeland

Hilton Vacation Club Mystic Dunes Orlando

Omni Orlando Resort at ChampionsGate

Embassy Suites By Hilton Orlando Sunset Walk

Ramada by Wyndham Davenport Orlando South

Hilton Vacation Club Aqua Sol Orlando West

Explore a world of travel with Expedia

Go further with the Expedia app

Lakeland - Winter Haven Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lakeland - Winter Haven holiday rentals

1. Lake Ida Beach Resort

2. BlockHaven near Legoland & Disney

3. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4. Vacation Village Orlando, Celebration

5. Barefoot'n Resort Kissimmee Orlando

6. Camp Mack Lodge, Marina & RV Resort

7. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

8. Upstay 3BR Condo w Pool & Patio Near Disney

9. Lifetime of Vacations Resort

Find holiday rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

The Berkley, Orlando

Explore a world of travel with Expedia

Go further with the Expedia app